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Silyl Group‐Directed 6‐ exo ‐ dig Iodocyclization of Homopropargylic Carbamates and Amides
Author(s) -
Okitsu Takashi,
Nakahigashi Hikaru,
Sugihara Ryosuke,
Fukuda Ikki,
Tsuji Saki,
In Yasuko,
Wada Akimori
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804794
Subject(s) - silylation , acetal , urea , chemistry , sulfide , group (periodic table) , dig , medicinal chemistry , organic chemistry , catalysis , computer science , world wide web
Iodocyclization of silyl group‐substituted homopropargylic carbamates and amides proceeded via 6‐ exo ‐ dig mode to afford 6‐vinylene‐4,5‐dihydro‐1,3‐oxazines in moderate to quantitative yields. This is the first report for silyl group‐solely directed iodocyclization of alkynes utilizing the β‐silyl effect. Under these mild reaction conditions, various functionalities such as secondary alcohol, acetal, urea, and sulfide were tolerated.